70877-75-7Relevant articles and documents
A Catalyst-Controlled Enantiodivergent Bromolactonization
Chan, Yuk-Cheung,Lam, Ying-Pong,Tse, Ying-Lung Steve,Wang, Xinyan,Wong, Jonathan,Yeung, Ying-Yeung
supporting information, p. 12745 - 12754 (2021/08/30)
A catalyst-controlled enantiodivergent bromolactonization of olefinic acids has been developed. Quinine-derived amino-amides bearing the same chiral core but different achiral aryl substituents were used as the catalysts. Switching the methoxy substituent in the aryl amide system from meta- to ortho-position results in a complete switch in asymmetric induction to afford the desired lactone in good enantioselectivity and yield. Mechanistic studies, including chemical experiments and density functional theory calculations, reveal that the differences in steric and electronic effects of the catalyst substituent alter the reaction mechanism.
Enantioselective 1,6-Conjugate Addition of Dialkyl α-Diazo Methylphosphonate to para-Quinone Methides
Chen, Yuan,Yu, Rui,Wang, Min,Huang, Yanmin,Peng, Yungui
supporting information, p. 4856 - 4861 (2021/09/06)
An asymmetric 1,6-conjugate addition reaction of dialkyl diazomethylphosphonates to para-quinone methides promoted by phase-transfer catalysis has been developed. A series of chiral diarylmethylated diazomethylphosphonates were accessed with up to 85% yields and 99% ee enantioselectivities. The resulting products were further transformed into bioactive compounds, namely, a chiral dihydrocinnoline phosphonate and a chiral α-aminophosphonate, bearing diarylmethine stereogenic centers. (Figure presented.).
Organocatalytic Nitroaldol Reaction Associated with Deuterium-Labeling
Yamada, Tsuyoshi,Kuwata, Marina,Takakura, Ryoya,Monguchi, Yasunari,Sajiki, Hironao,Sawama, Yoshinari
supporting information, p. 637 - 641 (2017/12/13)
A deuterium-labeling reaction of nitroalkanes in deuterium oxide and the subsequent nitroaldol reaction have been accomplished under basic and organocatalytic conditions to provide the deuterium-labeled β-nitroalcohols in high yields and high deuterium contents. β-Deuterated β-nitroalcohols could be smoothly obtained from the reaction of nitroalkanes and various electrophiles using the easily-removal basic resin WA30. Furthermore, the asymmetric nitroaldol reaction using nitromethane and α-keto esters as electrophiles in the presence of a quinine-derived organocatalyst in deuterium oxide could provide the desired β-deuterated nitroalcohol derivatives with high enantioselectivities. (Figure presented.).
